ES2570766T3 - Derivatives of 1-benzyl-3-hydroxymethylindazole and its use in the treatment of diseases based on the expression of MCP-1 and CX3CR1 - Google Patents

Derivatives of 1-benzyl-3-hydroxymethylindazole and its use in the treatment of diseases based on the expression of MCP-1 and CX3CR1

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ES2570766T3
ES2570766T3 ES09718101T ES09718101T ES2570766T3 ES 2570766 T3 ES2570766 T3 ES 2570766T3 ES 09718101 T ES09718101 T ES 09718101T ES 09718101 T ES09718101 T ES 09718101T ES 2570766 T3 ES2570766 T3 ES 2570766T3
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carbon atoms
hydrogen
alkyl group
group
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Angelo Guglielmotti
Guido Furlotti
Giorgina Mangano
Nicola Cazzolla
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Angelini Acraf SpA
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Aziende Chimiche Riunite Angelini Francesco ACRAF SpA
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Abstract

Compuesto de fórmula (I)**Fórmula** en el que: A puede ser -X1- o -X1-O-X2-, en el que X1 puede ser un grupo alquilo que presenta de 1 a 5 átomos de carbono, sustituido opcionalmente 10 con uno o más grupos alquilo que presentan de 1 a 5 átomos de carbono o uno o más grupos alcoxi que presentan de 1 a 3 átomos de carbono, y X2 puede ser un grupo alquilo que presenta de 1 a 5 átomos de carbono, sustituido opcionalmente con uno o más grupos alquilo que presentan de 1 a 5 átomos de carbono, Y puede ser hidrógeno, -OH, -N(R11)(R12), -N(R11)O(R12), en el que R11 puede ser hidrógeno, un grupo alquilo que presenta de 1 a 5 átomos de carbono, un grupo alcoxi que presenta de 1 a 3 átomos de carbono, o R11 junto con R12 forma un heterociclo de 4 a 7 miembros, R12 puede ser hidrógeno, un grupo alquilo que presenta de 1 a 5 átomos de carbono, un grupo alcoxi que presenta de 1 a 3 átomos de carbono, COR', COOR', CON(R')(R'') con R' y R'', que pueden ser iguales o diferentes entre sí, representados por hidrógeno y un grupo alquilo que presenta de 1 a 5 átomos de carbono, o R12 junto con R11 forma un heterociclo de 4 a 7 miembros, R1 y R2, que pueden ser iguales o diferentes entre sí, pueden ser hidrógeno, un grupo alquilo que presenta de 1 a 5 átomos de carbono, R3, R4 y R8, que pueden ser iguales o diferentes entre sí, pueden ser hidrógeno, un grupo alquilo que presenta de 1 a 5 átomos de carbono, un grupo alcoxi que presenta de 1 a 3 átomos de carbono, un átomo de halógeno, -OH, -N(R')(R''), -N(R')COR'', -CN, -CONR'R'', -SO2NR'R'', -SO2R', nitro y trifluorometilo; con R' y R'', que pueden ser iguales o diferentes entre sí, representados por hidrógeno y un grupo alquilo que presenta de 1 a 5 átomos de carbono, R5 puede ser hidrógeno, un grupo alquilo que presenta de 1 a 5 átomos de carbono, un grupo alcoxi que presenta de 1 a 3 átomos de carbono, un átomo de halógeno, -OH, -N(R')(R''), -N(R')COR'', nitro y trifluorometilo, o R5, junto con uno de entre R6 y R7, forma un anillo que presenta 5 o 6 átomos de carbono; con R' y R'', que pueden ser iguales o diferentes entre sí, representados por hidrógeno y un grupo alquilo que presenta de 1 a 5 átomos de carbono, R6 y R7, que pueden ser iguales o diferentes entre sí, pueden ser hidrógeno, un grupo alquilo que presenta de 1 a 5 átomos de carbono, o forman conjuntamente un grupo C>=O, o uno de entre R6 y R7, junto con R5, forma un anillo que presenta 5 o 6 átomos de carbono.Compound of formula (I) ** Formula ** in which: A can be -X1- or -X1-O-X2-, in which X1 can be an alkyl group having 1 to 5 carbon atoms, substituted optionally 10 with one or more alkyl groups having 1 to 5 carbon atoms or one or more alkoxy groups having 1 to 3 carbon atoms, and X2 may be an alkyl group having 1 to 5 carbon atoms, optionally substituted with one or more alkyl groups having 1 to 5 carbon atoms, Y may be hydrogen, -OH, -N (R11) (R12), -N (R11) O (R12), in which R11 can be hydrogen, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or R11 together with R12 forms a 4- to 7-membered heterocycle, R12 can be hydrogen, a group alkyl having 1 to 5 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, COR ', COOR', CON (R ') (R' ') with R' and R '', which can be the same or different from each other í, represented by hydrogen and an alkyl group having 1 to 5 carbon atoms, or R12 together with R11 forms a 4- to 7-membered heterocycle, R1 and R2, which may be the same or different from each other, may be hydrogen, an alkyl group having 1 to 5 carbon atoms, R3, R4 and R8, which may be the same or different from each other, may be hydrogen, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having from 1 to 3 carbon atoms, a halogen atom, -OH, -N (R ') (R' '), -N (R') COR '', -CN, -CONR'R '', -SO2NR 'R', -SO2R ', nitro and trifluoromethyl; with R 'and R' ', which may be the same or different from each other, represented by hydrogen and an alkyl group having 1 to 5 carbon atoms, R5 may be hydrogen, an alkyl group having 1 to 5 atoms of carbon, an alkoxy group having 1 to 3 carbon atoms, a halogen atom, -OH, -N (R ') (R' '), -N (R') COR '', nitro and trifluoromethyl, or R5, together with one of R6 and R7, forms a ring having 5 or 6 carbon atoms; with R 'and R' ', which may be the same or different from each other, represented by hydrogen and an alkyl group having 1 to 5 carbon atoms, R6 and R7, which may be the same or different from each other, may be hydrogen , an alkyl group having 1 to 5 carbon atoms, or together forming a group C> = O, or one of R6 and R7, together with R5, forms a ring having 5 or 6 carbon atoms.

ES09718101T 2008-03-07 2009-03-06 Derivatives of 1-benzyl-3-hydroxymethylindazole and its use in the treatment of diseases based on the expression of MCP-1 and CX3CR1 Active ES2570766T3 (en)

Applications Claiming Priority (2)

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EP08425141 2008-03-07
PCT/EP2009/052660 WO2009109654A2 (en) 2008-03-07 2009-03-06 Novel 1-benzyl-3-hydroxymethyilindazole derivatives and use thereof in the treatment of diseases based on the expression mcp-1 and cx3cr1

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US (2) US8314099B2 (en)
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JP (1) JP5509102B2 (en)
KR (1) KR101581829B1 (en)
CN (1) CN101959866B (en)
AR (1) AR070813A1 (en)
AU (1) AU2009221063B2 (en)
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CY (1) CY1117504T1 (en)
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EA (1) EA018185B1 (en)
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HK (1) HK1148271A1 (en)
HR (1) HRP20160457T1 (en)
HU (1) HUE026910T2 (en)
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CA2714436C (en) * 2008-03-07 2017-06-27 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Novel 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of mcp-1, cx3cr1 and p40
AU2009221089B2 (en) * 2008-03-07 2013-12-05 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Novel 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of MCP-1, CX3CR1 and p40
UA108742C2 (en) 2009-09-23 2015-06-10 PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF MCP-1 MEDIATED DISEASES
TWI543975B (en) * 2011-09-13 2016-08-01 Eisai R&D Man Co Ltd Pyrrolidin-3-yl acetic acid derivatives
US8476301B2 (en) 2011-09-13 2013-07-02 Eisai R&D Management Co., Ltd. Pyrrolidin-3-ylacetic acid derivative
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MX2014014657A (en) * 2012-06-01 2015-08-10 Nogra Pharma Ltd Bicyclic heterocycles capable of modulating t-cell responses, and methods of using same.
WO2014142056A1 (en) 2013-03-12 2014-09-18 エーザイ・アール・アンド・ディー・マネジメント株式会社 Salt of pyrrolidin-3-yl acetic acid derivative and crystals thereof
WO2014142086A1 (en) * 2013-03-13 2014-09-18 エーザイ・アール・アンド・ディー・マネジメント株式会社 Pyrrolidin-3-yl acetate derivative and piperidin-3-yl acetate derivative
CA2989270A1 (en) * 2015-06-16 2016-12-22 Translatum Medicus, Inc. Compositions and methods for treating and diagnosing ocular disorders
WO2020261158A1 (en) * 2019-06-25 2020-12-30 Translatum Medicus Inc. Processes of making 2-((1-benzyl-1h-indazol-3-yl)methoxy)-2-methylpropanoic acid and its derivatives

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CA2714436C (en) 2008-03-07 2017-06-27 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Novel 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of mcp-1, cx3cr1 and p40
AU2009221089B2 (en) 2008-03-07 2013-12-05 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Novel 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of MCP-1, CX3CR1 and p40
UA108742C2 (en) 2009-09-23 2015-06-10 PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF MCP-1 MEDIATED DISEASES

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CA2715065A1 (en) 2009-09-11
KR101581829B1 (en) 2015-12-31
EA018185B1 (en) 2013-06-28
HK1148271A1 (en) 2011-09-02
AU2009221063A1 (en) 2009-09-11
EP2262777B1 (en) 2016-02-24
WO2009109654A8 (en) 2010-06-03
CN101959866A (en) 2011-01-26
CY1117504T1 (en) 2017-04-26
JP5509102B2 (en) 2014-06-04
AR070813A1 (en) 2010-05-05
SI2262777T1 (en) 2016-05-31
CN101959866B (en) 2013-10-02
BRPI0908883A2 (en) 2015-09-15
KR20100131448A (en) 2010-12-15
WO2009109654A2 (en) 2009-09-11
MX2010009624A (en) 2010-09-28
WO2009109654A3 (en) 2010-03-11
DK2262777T3 (en) 2016-05-17
HRP20160457T1 (en) 2016-05-20
EA201071043A1 (en) 2011-02-28
IL207278A (en) 2014-11-30
EP2262777B8 (en) 2016-05-04
US8569297B2 (en) 2013-10-29
CA2715065C (en) 2017-06-27
US20130012510A1 (en) 2013-01-10
HUE026910T2 (en) 2016-07-28
US20100317618A1 (en) 2010-12-16
EP2262777A2 (en) 2010-12-22
UA101350C2 (en) 2013-03-25
AU2009221063B2 (en) 2013-03-21
US8314099B2 (en) 2012-11-20
IL207278A0 (en) 2010-12-30
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